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Apartments in Chestertown for Rent

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Jul 18 - Jul 20
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Aug 8 - Aug 10
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Sep 5 - Sep 7

Apartments in Chestertown

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Fridge, microwave, oven, stovetop

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (55)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Marina

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

10.0 out of 10, Exceptional, (50)
"Everything about our stay was outstanding. Beautiful, just like the pictures show. We highly recommend this property."
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (41)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Downtown furnished apartment - walking distance to restaurants
Interior

Downtown furnished apartment - walking distance to restaurants

10.0 out of 10, Exceptional, (5)
"The home is beautiful and exceptionally maintained! The management of the property is fantastic and they are lovely to work with. They thoughtfully had fresh fruit and some light & healthy munchies in the kitchen when I checked in. The history of the home is also quite interesting! I look forward to a return stay."
Downtown furnished apartment - walking distance to restaurants
Waterfront Retreat with Private Dock and Beach
Miscellaneous

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (21)
"Everything about the place was great! Easy check in and super clean and homey feeling spot. Would recommend to anyone looking for a quiet and comfy place on the eastern shore. We will definitely be booking again if we come back to the area!"
$341 nightly
The price is $376
Jul 10 - Jul 11
Total includes taxes and fees
Waterfront Retreat with Private Dock and Beach
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
1 bedroom, bed sheets

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (7)
"Located in a quite area and the host were incredible"
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (35)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

10.0 out of 10, Exceptional, (14)
$111 nightly
The price is $118
Jul 15 - Jul 16
Total includes taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Interior

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

9.6 out of 10, Exceptional, (30)
"Perfect place to go and relax and get away from the world. "
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Cozy Fells Point Gem / In The Heart of Fells Point
Marina

Cozy Fells Point Gem / In The Heart of Fells Point

9.8 out of 10, Exceptional, (191)
"Apartment was well appointed, we found everything we needed for a great stay. The place was super clean, check-in and check-out were simple and the location was perfect!"
$177 nightly
The price is $204
Jul 13 - Jul 14
Total includes taxes and fees
Cozy Fells Point Gem / In The Heart of Fells Point
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Miscellaneous

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (8)
"Perfection"
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Cozy 1st Floor King George one bedroom apartment right across from USNA
Fridge, microwave, oven, stovetop

Cozy 1st Floor King George one bedroom apartment right across from USNA

10.0 out of 10, Exceptional, (31)
"We were thrilled to be able to return to this great apartment.It is very close to Gate 1 and the sofa bed has a great mattress on it!We hope to continue to return to this rental."
Cozy 1st Floor King George one bedroom apartment right across from USNA
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Private kitchen

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

10.0 out of 10, Exceptional, (1)
"This property was decorated beautifully. Roomy and functional. We enjoyed coffee on the rear deck. Neighborhood restaurants were great. We had great communication with our host. This trip far exceeded our expectations."
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

9.6 out of 10, Exceptional, (7)
"Property description is accurate, host is quickly responsive."
18th Cent. Charm in Historic Downtown Annapolis
Spectacular Location: State Circle Apartment
Exterior

Spectacular Location: State Circle Apartment

10.0 out of 10, Exceptional, (12)
"Great location around the corner from our Thanksgiving celebration. "
Spectacular Location: State Circle Apartment
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Aerial view

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

10.0 out of 10, Exceptional, (2)
"We stayed for a night ahead of a local festival. While my husband and I had travel issues and got in super late, my in-laws really enjoyed the property. Very clean and convenient to everything. We will stay again. Thank you!"
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Walk everywhere from 1st floor dog-friendly apartment with parking and backyard
Fridge, microwave, oven, stovetop

Walk everywhere from 1st floor dog-friendly apartment with parking and backyard

2.5 star property
10.0 out of 10, Exceptional, (2)
"This tastefully decorated apartment is in a perfect location to enjoy all that is Annapolis. "
Walk everywhere from 1st floor dog-friendly apartment with parking and backyard
Bel Air Apartment w/ Pool ~ 2 Mi to Main St
Property grounds

Bel Air Apartment w/ Pool ~ 2 Mi to Main St

Bel Air Apartment w/ Pool ~ 2 Mi to Main St
Charming Eastport
Fridge, microwave, stovetop, coffee/tea maker

Charming Eastport

9.4 out of 10, Exceptional, (3)
"We thoroughly enjoyed this section of Eastport. The views of the marina were beautiful and we found a couple new restaurants nearby! Excellent communication with the owners."
Charming Eastport
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (73)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
$434 nightly
The price is $495
Jul 16 - Jul 17
Total includes taxes and fees
Waterfront Oasis of Annapolis Star
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 7 apartments in Chestertown for your vacation.
Why should you consider apartments instead of traditional hotels?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, and also for families wanting the conveniences of home.
What's the top apartment for my stay in Chestertown?
First Floor Studio Apartment in Historic Chestertown: Includes a private pool, laundry facilities, and free WiFi. A fitness center and onsite laundry facilities are on site. Historic Downtown Garden Oasis with Private Patio: Free WiFi, outdoor space, and separate dining areas are included.
How many apartments can I expect to find in Chestertown?
Expedia has 7 apartments to book in Chestertown.
What can I expect from the weather during my trip to Chestertown?
Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Chestertown. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What should I see and do in Chestertown?
Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Chestertown Dog Park and Urieville Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Rolphs Wharf Marina and Chestertown Historic District.
What's the best way to get to and around Chestertown?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the heart of the city. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.